Mr Chan Chun Sing will never forget the three families who turned up to ask for help at his Meet-the-People Sessions.
One of them earned just $2,000 a month, but managed to raise three children. Another had double that income, of $4,000 to $5,000, and had no children.
But it was the third, a family that earned $16,000 and had two children, who complained the most, saying the Government was not doing enough to help them.
The incident, says Mr Chan, illustrates the rising expectations that Singaporeans have and the challenge that policymakers face as they try to work out who should get more help.
"It's not an easy question to answer and we will have to find the answer as a society going forward," he says.
It is also a challenge Mr Chan's new ministry, the Ministry of Social and Family Development (MSF), will have to grapple with as it streamlines its responsibilities to focus more on policies affecting Singaporean families.
On Thursday, the Ministry of Community Development, Youth and Sports (MCYS) will be renamed the MSF and pass on its youth and sports portfolios to the newly created Ministry of Culture, Community and Youth.
That will give Mr Chan's ministry more time and space to look at longer-term challenges such as meeting the needs of singles when they age in 20 years' time and finding ways to tap the energies of healthy elderly people to serve other senior citizens.
At an hour-long interview at the MCYS headquarters in Toa Payoh this week, the Acting Minister laid out the priorities for his new ministry.
One of them will be to strengthen the social safety net - which will require the ministry to factor in Singaporeans' changing expectations. Another is to improve the delivery of social services, and a third is to strengthen families.
Mr Chan notes that it is no longer only those at the bottom of the ladder who need help. Those in the middle are starting to feel unsettled by the growing income gap too.
"They wonder whether they can meet their aspirations because of the people at the top end," he says.
"The question for us is, as a society, to what extent we can actually help this group of people beyond the people at the bottom of the socio-economic scale."
As economic cycles become shorter and more volatile, people are also more likely to be in and out of jobs, he observes. They will have to relearn their skills at a much faster rate as well.
"If I use my mother as an example, she was a machine operator, stamping metal plates. She did that for at least 30 years."
With just one set of skills, notes Mr Chan, his mother, a divorcee, was able to raise him and his sister single-handedly.
But no longer.
The churn in jobs and the instability of people's incomes today pose a serious challenge and could even disrupt the way children are brought up and their education.
Another concern for Mr Chan is Singapore's changing demographics: More people are staying single, marrying later, having fewer children and living longer.
As he looks into the next 10 to 15 years, he foresees a shrinking of the support that extended families can now give in raising children and caring for sick relatives.
"So that is where you see us... not just building the nursing homes, which are institutional care, but growing the community care sector and the home care services," he says.
Strengthening elderly care services in the community and at home will allow people to grow old in familiar settings, he explains.
Longevity will pose another challenge as people in their 80s and 90s will be increasingly cared for by those in their 50s and 60s.
But Mr Chan also sees these healthy retirees as a source of volunteers and helpers to beef up the delivery of social services at the local level, as is being done in Japan.
Singapore is now trying out this idea: Lions Befrienders, for instance, is getting the old to befriend the old, while a seniors' activity centre in Choa Chu Kang pays elderly folk a stipend to run activities.
As for the larger challenge of strengthening families, Mr Chan thinks measures should be targeted at people's four life stages: when they are young, when they marry, when they have children and when they are maintaining a family.
He believes that a central plank of the efforts - besides helping couples with housing, health care, childcare and education - should be to inculcate from young values for marriage, parenthood and family.
"If we bring up our children appreciating the joy of a family, then I think when they grow up, chances are that they will also aspire to have their own family," he says.
It means getting people not to see their career as an obstacle to starting a family, helping them to appreciate the joy of parenthood, and maintaining healthy relationships between parents and teenagers.
Such values can be transmitted through schools and the media, he says, especially as children may not live with their grandparents and parents may be working. Positive role models are also needed, he adds.
The 43-year-old says his own values were shaped by his family and the people he met. Watching Hong Kong sword-fighting drama serials and movies helped, he quips.
The former army chief married his colleague in Mindef in 1997 at the age of 28 - the median age then. They have three children, aged 11, three and one.
Recalling their decision to wed and have children, he cites a senior's advice: "He told me that there's never a perfect time to get married or to have a child... The perfect time is when you have the commitment to overcome life's challenges with your partner.
"But through the whole journey, you find a new sense of joy and purpose beyond just the pursuit of material well-being for yourself."
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